Fucosterol
Basic information
- CAS
17605-67-3- Standard SMILES
C/C=C(\CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C- InChIKey
OSELKOCHBMDKEJ-JUGJNGJRSA-N- Molecular formula
- C29H48O
- Average molar mass
- 412.7 g/mol
- Monoisotopic mass
- 412.37051615
Overview
Fucosterol is a 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). It has a role as an antioxidant, a metabolite and a hepatoprotective agent. It is a 3beta-hydroxy-Delta(5)-steroid, a C29-steroid, a member of phytosterols and a 3beta-sterol. It derives from a hydride of a stigmastane.
Names & identifiers
- Preferred name
- Fucosterol
- IUPAC
- (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- English name
- FUCOSTEROL
- Molecular formula
- C29H48O
- Molecular weight
- 412.69
Names & synonyms
Fucosterol17605-67-3Fucosterin(24E)-24-N-Propylidenecholesteroltrans-24-EthylidenecholesterolStigmasta-5,24(28)-dien-3-ol, (3beta,24E)-(24E)-stigmasta-5,24(28)-dien-3beta-ol(3beta,24E)-Stigmasta-5,24(28)-dien-3-ol504ZAM710CDTXSID70103322924E-ethylidene-cholest-5-en-3beta-ol(E)-Stigmasta-5,24(28)-dien-3beta-ol
Show more names
Aids113090-17-((R,E)Aids-113090Fucosterol (AS)28-IsofucosterolFUCOSTEROL(AS) 5mgFUCOSTEROL,17605-67-3Fucosterol (Standard)
CHEBI:27865(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol(3beta,24E)-stigmasta-5,24(28)-dien-olstigmasta-5,24-dien-3 beta-ol(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((E,2R)-5-propan-2-ylhept-5-en-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol24Z-ethylidenecholest-5-en-3B-olRefChem:14158924-isoethylidenecholest-5-en-3 beta-ol,delta(5)-avenasterol
Database identifiers
- CAS
17605-67-3- PubChem CID
- 5281328
- DTXSID
DTXSID701033229- ChEMBL
CHEMBL519971- ChEBI
CHEBI:27865- UNII
- 504ZAM710C
- Nikkaji
- J9.102B
Properties
Computed structural properties
- XLogP
- 8.9
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 686
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Stigmasterols and C24-ethyl derivatives [ST0104]
Physicochemical properties
- Melting point
- 118 · 118-120°C
- alpha
- 20 · D20 -38.4° (chloroform)
- Boiling point
- 220 · 220-230 °C
- Density
- 0.98 · 0.98±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 15.03 · 15.03±0.70(Predicted)
- color
- White to Off-White
- Cosmetics Ingredients Functions
- HAIR CONDITIONINGSKIN PROTECTINGSKIN CONDITIONING - EMOLLIENTSKIN CONDITIONINGANTIOXIDANT
- InChI
- 1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+
- InChIKey
- OSELKOCHBMDKEJ-QDNKTFMZNA-N
- SMILES
- [C@@]12([H])CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])[C@H](C)CC/C(=C/C)/C(C)C |&1:0,6,10,12,16,18,21,23,r|
- LogP
- 10.41 · 10.410 (est)
- FDA UNII
- 504 ZAM710C · 504ZAM710C
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
UsesFucosterol is a steroid for proteomics research.
Additional notes
DefinitionChEBI: A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28).
Related reactions
1 records
Compound notes
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